2-[(R)-Hydr­oxy(6-methoxy­quinolinium-4-yl)meth­yl]-8-vinyl-1-azoniabicyclo­[2.2.2]octane tetra­chloridoferrate(III) chloride monohydrate

Chen, L.-Z.; Huang, M.-N.

doi:10.1107/S1600536810007889

2-[(R)-Hydroxy(6-methoxyquinolinium-4-yl)methyl]-8-vinyl-1-azoniabicyclo[2.2.2]octane tetrachloridoferrate(III) chloride monohydrate

In the title salt, (C₂₀H₂₆N₂O₂)[FeCl₄]Cl·H₂O, the Fe^III atom exists in a tetrahedral coordination environment. The cation, anions and water molecules are linked by N—H

Cl, O—H

Cl and O—H

O hydrogen bonds into a layer network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810007889/ng2725sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810007889/ng2725Isup2.hkl Contains datablock I

CCDC reference: 774120

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.048
wR factor = 0.118
Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          7
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of         Fe1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               5166
           Count of symmetry unique reflns         2681
           Completeness (_total/calc)            192.69%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2485
           Fraction of Friedel pairs measured     0.927
           Are heavy atom types Z>Si present        yes
PLAT917_ALERT_2_G The FCF is likely NOT based on a BASF/TWIN Flack          !
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT791_ALERT_4_G The Model has Chirality at N2      (Verify) ....          S
PLAT791_ALERT_4_G The Model has Chirality at C11     (Verify) ....          R
PLAT791_ALERT_4_G The Model has Chirality at C12     (Verify) ....          S
PLAT791_ALERT_4_G The Model has Chirality at C14     (Verify) ....          S
PLAT791_ALERT_4_G The Model has Chirality at C18     (Verify) ....          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The existence of a chiral centre in an organic ligand is very important for the construction noncentrosymmetric or chiral coordination polymers that exhibit desirable physical properties such as ferroelectricity (Fu et al., 2007), Chiral quinine has a chiral centre which have shown tremendous scope in the synthesis of transition-metal complexes (Zhao et al., 2003; Qu et al.,2003). The construction of new members of this family of ligands is an important direction in the development of modern coordination chemistry. We report here the crystal structure of the title compound

The asymmetric unit of the title compound,C₂₀H₂₆N₂O₂.FeCl₄.Cl.H₂O(Fig.1), consists of one protoned quinine and a tetrachloro-ironanion with the Fe^III ion in a slightly distorted tetrahedral coordination environment, The crystal structure is stabilized by intermolecular N—H···Cl, O—H···Cl and O—H···O hydrogen bonds.The H-bonds form of1D chain viewedalong the a-axis (Fig.2).

Related literature top

For ferroelectricity and SHG, see: Fu et al. (2007); Qu et al. (2003). For related transition-metal complexes, see: Zhao et al. (2003).

Experimental top

A mixture of quinine (1 mmol, 0.324 g ), FeCl₃(1 mmol, 0.156 g) and 10% aqueous HCl (6 ml) were mixed and dissolved in 20 ml water by heating to 353 K (0.5 h) forming a clear solution. The reaction mixture was cooled slowly to room temperature, crystals of the title compound were formed after 11 days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with atom labels. Displacement ellipsoids were drawn at the 30% probability level. Hydrogen atoms have been omitted for clarity_.
	Fig. 2. The packing viewed along the c axis. Hydrogen bonds are drawn as dashed lines

2-[(R)-Hydroxy(6-methoxyquinolinium-4-yl)methyl]-8-vinyl-1- azoniabicyclo[2.2.2]octane tetrachloridoferrate(III) chloride monohydrate top

Crystal data top

(C₂₀H₂₆N₂O₂)[FeCl₄]Cl·H₂O	F(000) = 594
M_r = 577.54	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3650 reflections
a = 6.6838 (10) Å	θ = 2.9–26.0°
b = 18.843 (2) Å	µ = 1.10 mm⁻¹
c = 10.8716 (10) Å	T = 293 K
β = 104.918 (17)°	Block, yellow
V = 1323.1 (3) Å³	0.30 × 0.26 × 0.22 mm
Z = 2

Data collection top

Rigaku SCXmini diffractometer	5166 independent reflections
Radiation source: fine-focus sealed tube	3650 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 13.6612 pixels mm^-1	θ_max = 26.0°, θ_min = 2.9°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −23→23
T_min = 0.82, T_max = 0.88	l = −13→13
12145 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0558P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
5166 reflections	Δρ_max = 0.32 e Å⁻³
281 parameters	Δρ_min = −0.30 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2490 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Crystal data top

(C₂₀H₂₆N₂O₂)[FeCl₄]Cl·H₂O	V = 1323.1 (3) Å³
M_r = 577.54	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.6838 (10) Å	µ = 1.10 mm⁻¹
b = 18.843 (2) Å	T = 293 K
c = 10.8716 (10) Å	0.30 × 0.26 × 0.22 mm
β = 104.918 (17)°

Data collection top

Rigaku SCXmini diffractometer	5166 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3650 reflections with I > 2σ(I)
T_min = 0.82, T_max = 0.88	R_int = 0.038
12145 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.118	Δρ_max = 0.32 e Å⁻³
S = 1.01	Δρ_min = −0.30 e Å⁻³
5166 reflections	Absolute structure: Flack (1983), 2490 Friedel pairs
281 parameters	Absolute structure parameter: 0.01 (2)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1691 (8)	0.4587 (3)	0.0478 (5)	0.0721 (13)
H1A	0.0700	0.4306	0.0706	0.087*
C2	0.2105 (7)	0.5255 (3)	0.0993 (4)	0.0631 (11)
H2A	0.1359	0.5426	0.1544	0.076*
C3	0.3610 (6)	0.5673 (2)	0.0701 (4)	0.0520 (10)
C4	0.4661 (6)	0.5415 (2)	−0.0214 (4)	0.0508 (9)
C5	0.4159 (7)	0.4721 (3)	−0.0707 (4)	0.0623 (11)
C6	0.5180 (8)	0.4417 (3)	−0.1549 (4)	0.0762 (14)
H6A	0.4841	0.3962	−0.1865	0.091*
C7	0.6682 (8)	0.4797 (3)	−0.1902 (4)	0.0750 (14)
H7A	0.7391	0.4595	−0.2447	0.090*
C8	0.7173 (8)	0.5502 (3)	−0.1442 (4)	0.0646 (12)
C9	0.6189 (7)	0.5800 (2)	−0.0622 (3)	0.0567 (10)
H9A	0.6521	0.6260	−0.0327	0.068*
C10	0.9150 (9)	0.6537 (3)	−0.1527 (5)	0.0857 (16)
H10A	1.0218	0.6701	−0.1901	0.129*
H10B	0.9624	0.6567	−0.0616	0.129*
H10C	0.7938	0.6826	−0.1818	0.129*
C11	0.4201 (6)	0.6379 (2)	0.1375 (3)	0.0508 (9)
H11A	0.4540	0.6721	0.0781	0.061*
C12	0.6126 (6)	0.62488 (19)	0.2487 (3)	0.0467 (9)
H12A	0.7089	0.5959	0.2156	0.056*
C13	0.5696 (7)	0.5844 (2)	0.3628 (4)	0.0565 (10)
H13A	0.4229	0.5861	0.3583	0.068*
H13B	0.6098	0.5351	0.3601	0.068*
C14	0.6917 (7)	0.6182 (3)	0.4861 (4)	0.0622 (11)
H14A	0.6783	0.5893	0.5585	0.075*
C15	0.6009 (9)	0.6922 (3)	0.4946 (5)	0.0815 (14)
H15A	0.4575	0.6881	0.4976	0.098*
H15B	0.6774	0.7157	0.5718	0.098*
C16	0.6143 (8)	0.7356 (3)	0.3786 (5)	0.0770 (14)
H16A	0.4763	0.7477	0.3285	0.092*
H16B	0.6894	0.7793	0.4058	0.092*
C17	0.9372 (7)	0.6747 (3)	0.3784 (4)	0.0672 (12)
H17A	1.0108	0.7180	0.4108	0.081*
H17B	1.0137	0.6506	0.3261	0.081*
C18	0.9227 (7)	0.6269 (3)	0.4897 (4)	0.0667 (12)
H18A	0.9909	0.6513	0.5689	0.080*
C19	1.0326 (9)	0.5569 (3)	0.4871 (6)	0.0859 (16)
H19A	0.9833	0.5274	0.4172	0.103*
C20	1.1894 (11)	0.5353 (4)	0.5747 (7)	0.126 (3)
H20A	1.2428	0.5634	0.6459	0.151*
H20B	1.2493	0.4915	0.5667	0.151*
N1	0.2684 (6)	0.4343 (2)	−0.0331 (4)	0.0677 (10)
H1B	0.2353	0.3875	−0.0673	0.081*
N2	0.7244 (6)	0.69263 (18)	0.2997 (3)	0.0574 (9)
H2C	0.7373	0.7211	0.2289	0.069*
O1	0.8655 (5)	0.5813 (2)	−0.1892 (3)	0.0807 (10)
O2	0.2546 (5)	0.66425 (17)	0.1827 (3)	0.0638 (8)
H2B	0.2211	0.7051	0.1509	0.096*
Cl5	0.2012 (3)	0.27667 (8)	−0.07702 (16)	0.1153 (6)
Cl3	0.8401 (4)	0.35869 (11)	0.53267 (16)	0.1329 (7)
Cl4	0.6722 (3)	0.24251 (8)	0.26529 (17)	0.1000 (5)
Cl2	0.3307 (3)	0.37297 (11)	0.3350 (2)	0.1408 (9)
Fe1	0.64976 (11)	0.35002 (3)	0.33590 (7)	0.0748 (2)
Cl1	0.7554 (2)	0.42527 (7)	0.21006 (13)	0.0801 (4)
O3	0.2399 (9)	0.7902 (3)	0.0442 (6)	0.156 (2)
H3B	0.1900	0.8190	0.0887	0.234*
H3A	0.1429	0.7743	−0.0162	0.234*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.073 (3)	0.061 (3)	0.081 (3)	−0.006 (2)	0.017 (3)	−0.003 (3)
C2	0.062 (3)	0.068 (3)	0.064 (3)	0.005 (2)	0.026 (2)	−0.002 (2)
C3	0.056 (2)	0.056 (2)	0.043 (2)	0.0083 (18)	0.0107 (19)	0.0022 (18)
C4	0.056 (2)	0.052 (2)	0.040 (2)	0.0091 (18)	0.0052 (19)	0.0009 (18)
C5	0.070 (3)	0.065 (3)	0.048 (2)	0.010 (2)	0.008 (2)	0.000 (2)
C6	0.089 (4)	0.073 (3)	0.065 (3)	0.011 (3)	0.017 (3)	−0.015 (3)
C7	0.083 (4)	0.094 (4)	0.045 (2)	0.018 (3)	0.012 (3)	−0.015 (2)
C8	0.075 (3)	0.082 (3)	0.038 (2)	0.010 (2)	0.015 (2)	−0.004 (2)
C9	0.068 (3)	0.064 (3)	0.038 (2)	0.005 (2)	0.013 (2)	−0.0013 (19)
C10	0.090 (4)	0.110 (5)	0.063 (3)	−0.019 (3)	0.033 (3)	0.002 (3)
C11	0.060 (3)	0.051 (2)	0.042 (2)	0.0082 (18)	0.0150 (19)	0.0027 (18)
C12	0.059 (2)	0.0405 (19)	0.0438 (19)	0.0040 (16)	0.0192 (18)	−0.0006 (16)
C13	0.056 (2)	0.065 (3)	0.046 (2)	−0.003 (2)	0.0091 (19)	0.010 (2)
C14	0.063 (3)	0.080 (3)	0.044 (2)	0.002 (2)	0.014 (2)	0.009 (2)
C15	0.095 (4)	0.083 (4)	0.073 (3)	0.011 (3)	0.034 (3)	−0.015 (3)
C16	0.094 (4)	0.056 (3)	0.080 (3)	0.010 (2)	0.020 (3)	−0.019 (2)
C17	0.065 (3)	0.073 (3)	0.064 (3)	−0.012 (2)	0.017 (2)	−0.004 (2)
C18	0.063 (3)	0.079 (3)	0.049 (2)	0.002 (2)	−0.003 (2)	−0.010 (2)
C19	0.068 (3)	0.087 (4)	0.094 (4)	0.002 (3)	0.006 (3)	0.001 (3)
C20	0.107 (5)	0.117 (5)	0.140 (6)	0.028 (4)	0.006 (5)	0.027 (5)
N1	0.076 (3)	0.053 (2)	0.071 (2)	−0.0045 (19)	0.012 (2)	−0.006 (2)
N2	0.069 (2)	0.0482 (19)	0.057 (2)	−0.0006 (16)	0.0193 (18)	0.0030 (16)
O1	0.085 (2)	0.109 (3)	0.0543 (18)	−0.005 (2)	0.0304 (17)	−0.0106 (19)
O2	0.0635 (18)	0.0644 (19)	0.0641 (17)	0.0230 (15)	0.0178 (15)	−0.0030 (15)
Cl5	0.1995 (19)	0.0617 (8)	0.1125 (12)	0.0004 (9)	0.0904 (13)	−0.0178 (8)
Cl3	0.201 (2)	0.1015 (12)	0.0886 (10)	0.0237 (14)	0.0246 (11)	0.0161 (10)
Cl4	0.1138 (11)	0.0722 (8)	0.1292 (13)	0.0163 (8)	0.0588 (10)	0.0050 (8)
Cl2	0.1171 (13)	0.1379 (16)	0.203 (2)	0.0635 (11)	0.1064 (14)	0.0824 (15)
Fe1	0.0851 (5)	0.0634 (4)	0.0877 (5)	0.0254 (4)	0.0437 (4)	0.0243 (4)
Cl1	0.0798 (8)	0.0780 (8)	0.0897 (8)	0.0127 (6)	0.0352 (7)	0.0281 (7)
O3	0.163 (5)	0.090 (3)	0.211 (6)	0.004 (3)	0.040 (4)	0.019 (4)

Geometric parameters (Å, º) top

C1—N1	1.314 (6)	C13—H13B	0.9700
C1—C2	1.377 (7)	C14—C15	1.533 (7)
C1—H1A	0.9300	C14—C18	1.543 (7)
C2—C3	1.378 (6)	C14—H14A	0.9800
C2—H2A	0.9300	C15—C16	1.525 (7)
C3—C4	1.442 (6)	C15—H15A	0.9700
C3—C11	1.521 (6)	C15—H15B	0.9700
C4—C9	1.414 (6)	C16—N2	1.503 (6)
C4—C5	1.420 (6)	C16—H16A	0.9700
C5—N1	1.362 (6)	C16—H16B	0.9700
C5—C6	1.397 (6)	C17—N2	1.497 (6)
C6—C7	1.367 (7)	C17—C18	1.531 (7)
C6—H6A	0.9300	C17—H17A	0.9700
C7—C8	1.428 (7)	C17—H17B	0.9700
C7—H7A	0.9300	C18—C19	1.513 (7)
C8—O1	1.346 (6)	C18—H18A	0.9800
C8—C9	1.358 (6)	C19—C20	1.288 (8)
C9—H9A	0.9300	C19—H19A	0.9300
C10—O1	1.435 (7)	C20—H20A	0.9300
C10—H10A	0.9600	C20—H20B	0.9300
C10—H10B	0.9600	N1—H1B	0.9599
C10—H10C	0.9600	N2—H2C	0.9601
C11—O2	1.411 (5)	O2—H2B	0.8499
C11—C12	1.541 (5)	Cl3—Fe1	2.196 (2)
C11—H11A	0.9800	Cl4—Fe1	2.1852 (16)
C12—N2	1.511 (5)	Cl2—Fe1	2.1734 (17)
C12—C13	1.545 (5)	Fe1—Cl1	2.2085 (13)
C12—H12A	0.9800	O3—H3B	0.8501
C13—C14	1.517 (6)	O3—H3A	0.8499
C13—H13A	0.9700

N1—C1—C2	120.6 (5)	C15—C14—C18	108.1 (4)
N1—C1—H1A	119.7	C13—C14—H14A	109.7
C2—C1—H1A	119.7	C15—C14—H14A	109.7
C1—C2—C3	120.8 (4)	C18—C14—H14A	109.7
C1—C2—H2A	119.6	C16—C15—C14	109.2 (4)
C3—C2—H2A	119.6	C16—C15—H15A	109.8
C2—C3—C4	118.7 (4)	C14—C15—H15A	109.8
C2—C3—C11	120.2 (4)	C16—C15—H15B	109.8
C4—C3—C11	121.0 (4)	C14—C15—H15B	109.8
C9—C4—C5	118.3 (4)	H15A—C15—H15B	108.3
C9—C4—C3	124.2 (4)	N2—C16—C15	108.9 (4)
C5—C4—C3	117.5 (4)	N2—C16—H16A	109.9
N1—C5—C6	119.7 (5)	C15—C16—H16A	109.9
N1—C5—C4	119.2 (4)	N2—C16—H16B	109.9
C6—C5—C4	121.1 (5)	C15—C16—H16B	109.9
C7—C6—C5	119.1 (5)	H16A—C16—H16B	108.3
C7—C6—H6A	120.4	N2—C17—C18	109.9 (4)
C5—C6—H6A	120.4	N2—C17—H17A	109.7
C6—C7—C8	120.6 (4)	C18—C17—H17A	109.7
C6—C7—H7A	119.7	N2—C17—H17B	109.7
C8—C7—H7A	119.7	C18—C17—H17B	109.7
O1—C8—C9	125.8 (5)	H17A—C17—H17B	108.2
O1—C8—C7	113.7 (4)	C19—C18—C17	111.6 (4)
C9—C8—C7	120.5 (5)	C19—C18—C14	113.2 (4)
C8—C9—C4	120.3 (4)	C17—C18—C14	108.0 (4)
C8—C9—H9A	119.8	C19—C18—H18A	107.9
C4—C9—H9A	119.8	C17—C18—H18A	107.9
O1—C10—H10A	109.5	C14—C18—H18A	107.9
O1—C10—H10B	109.5	C20—C19—C18	124.7 (6)
H10A—C10—H10B	109.5	C20—C19—H19A	117.7
O1—C10—H10C	109.5	C18—C19—H19A	117.7
H10A—C10—H10C	109.5	C19—C20—H20A	120.0
H10B—C10—H10C	109.5	C19—C20—H20B	120.0
O2—C11—C3	110.2 (4)	H20A—C20—H20B	120.0
O2—C11—C12	110.7 (3)	C1—N1—C5	123.2 (4)
C3—C11—C12	107.4 (3)	C1—N1—H1B	118.4
O2—C11—H11A	109.5	C5—N1—H1B	118.4
C3—C11—H11A	109.5	C17—N2—C16	109.1 (3)
C12—C11—H11A	109.5	C17—N2—C12	109.1 (3)
N2—C12—C11	112.8 (3)	C16—N2—C12	113.4 (4)
N2—C12—C13	107.4 (3)	C17—N2—H2C	108.4
C11—C12—C13	114.7 (3)	C16—N2—H2C	108.4
N2—C12—H12A	107.2	C12—N2—H2C	108.4
C11—C12—H12A	107.2	C8—O1—C10	116.8 (4)
C13—C12—H12A	107.2	C11—O2—H2B	109.0
C14—C13—C12	109.5 (3)	Cl2—Fe1—Cl4	109.81 (9)
C14—C13—H13A	109.8	Cl2—Fe1—Cl3	108.14 (9)
C12—C13—H13A	109.8	Cl4—Fe1—Cl3	109.65 (7)
C14—C13—H13B	109.8	Cl2—Fe1—Cl1	109.82 (6)
C12—C13—H13B	109.8	Cl4—Fe1—Cl1	108.41 (6)
H13A—C13—H13B	108.2	Cl3—Fe1—Cl1	111.00 (8)
C13—C14—C15	107.7 (4)	H3B—O3—H3A	109.5
C13—C14—C18	112.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl5	0.96	2.10	3.023 (4)	161
N2—H2C···Cl5ⁱ	0.96	2.08	3.039 (4)	173
O2—H2B···O3	0.85	2.00	2.799 (6)	156
O3—H3B···Cl5ⁱⁱ	0.85	2.71	3.070 (6)	108

Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	(C₂₀H₂₆N₂O₂)[FeCl₄]Cl·H₂O
M_r	577.54
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	6.6838 (10), 18.843 (2), 10.8716 (10)
β (°)	104.918 (17)
V (Å³)	1323.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.10
Crystal size (mm)	0.30 × 0.26 × 0.22

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.82, 0.88
No. of measured, independent and observed [I > 2σ(I)] reflections	12145, 5166, 3650
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.118, 1.01
No. of reflections	5166
No. of parameters	281
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.30
Absolute structure	Flack (1983), 2490 Friedel pairs
Absolute structure parameter	0.01 (2)

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).